The great challenge with teaching game design is the balance between theory and design. Like other digital humanities disciplines, learning about games requires active engagement with the object. This includes both games as sites of play and games as sites of design. Participants must play games and make games as much as possible. Through active inquiry with the object, a participant begins to engage with the theory behind games. To facilitate this process, we created a card game called Root of Play that guides participants through the game design process. Root of Play is different from other game-design games because it speciﬁcally emphasizes playable prototypes and design iterations. We found this focus on prototyping and playtesting allows participants to enter an agile process, moving between game theory and game building. We can summarize this agile design process as the negotiation between making and breaking. In this chapter, we explore the card game Root of Play as a case study for teaching games to digital humanists.